28. "The Grown-Ups" (Season 3, Episode 12)

Roger Sterling's daughter has her wedding — the day after November 22, 1963. No, it doesn't go well. The JFK news footage is chilling: Walter Cronkite fumbling with his glasses as he reads the death bulletin, the ominous reports about Adlai Stevenson and Gen. Edwin Walker in the background. The wedding guests sneak off to watch TV in the kitchen. Yet with so much tragedy in the air, Roger still manages to give the coolest wedding toast of all time.

Best line: "He was so handsome and now I'll never get to vote for him!"–Jane Siegel Sterling